Molecular Geometry as a Source of chemical Information. Part I: How H-Bonding Modifies Molecular Structure in the Vicinity of Hydrogen Donating Group. The Case of Phenol Derivatives Interacting with Nitrogen and Oxygen Bases

• Autorzy: Szatyłowicz H. , Krygowski T.
• Języki publikacji: EN

Abstrakty

EN

Analysis of geometrical patterns of 635 variously substituted phenols in H-bonding complexes with bases revealed that C1O, C1C2, C1C6 bond lengths as well as ipso bond angle change regularly with variation of the acidity (pKa) of phenols. The Bent-Walsh rule is fulfilled and the approximate linear dependence between the above mentioned geometry parameters works. The perturbation in the OH group, due to H-bonding, is transmitted even on further fragments of the ring. DFT modelling at the B3LYP/6-311+G** level of theory for the simplest cases illustrate nicely the conclusion derived for variously substituted systems.

Słowa kluczowe

EN

hydrogen bond; substituted phenols; Bent-Walsh rule

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2004
• Tom: Vol. 78 / nr 9
• Strony: 1719--1731

Twórcy

autor

Szatyłowicz H.

autor

Krygowski T.

• Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland

Bibliografia

• 1. Hoffmann R, foreword to Determination of the Geometrical Structure of Free Molecules, by Vilkov L.V., Mastryukov V.S., Sadova NX, Mir Publisher, Moscow, 1983; Russian version, Moscow, 1978.
• 2. Bernstein J., In: Accurate Molecular Structures, Their Determination and Importance, Domenicano A., Hargittai I., Eds.; Intern. Union of Crystallography, Oxford University Press, 1992; Chapt. 19, pp. 469-497.
• 3. Bürgi H.B., Angew. Chem., 87, 461 (1975).
• 4. Bürgi H.B., Inorg. Chem., 12, 2321 (1973).
• 5. Kaftory M. and Dunitz J.D., Acta Cryst., B31, 2912 (1975); Acta Cryst., B32, 1 (1976).
• 6. Dunitz J .D., X-ray Analysis and the Structure of Organic Molecules, Cornell University Press, 1978 pp 301-390.
• 7. Bügi H.B. and Dunitz J.D., In: Structure Correlation, Bürgi H.B., Dunitz J.D. Eds.; VCH, Weinheim, 1994; Vol. I, pp. 163-204.
• 8. Cieplak A.S., In: Structure Correlation, Bürgi H.B., Dunitz J.D. Eds.; VCH, Weinheim, 1994; Vol. I pp 205-302.
• 9. Bürgi H.B. and Szklover V., In: Structure Correlation, Bürgi H.B., Dunitz J.D. Eds.; VCH, Weinheim, 1994; Vol. I, pp. 303-335.
• 10. Bernstein J., Etter M.C. and Leiserowitz L., In: Structure Correlation, Bürgi H.-B., Dunitz J.D. Eds.; VCH, Weinheim, 1994;Vol II, pp. 431-507.
• 11. Klebe G., In: Structure Correlation, Bürgi H.B., Dunitz J.D. Eds.; VCH, Weinheim, 1994; Vol. II pp. 543-603.
• 12. Krygowski T.M. and Turowska-Tyrk I., Chem. Phys. Lett., 138, 90 (1987).
• 13. Domenicano A., Vaciago A. and Coulson C.A., Acta Cryst., B31, 221 and 1630 (1975).
• 14. Walsh A.D., Discuss. Faraday Soc., 2, 18 (1947).
• 15. Bent H.A., Chem. Rev., 61, 275 (1961).
• 16. Gillespie R.J., Molecular Geometry, Van Norstand: London, 1972.
• 17. Domenicano A., Mazzeo P. and Vaciago A., Tetrahedron Letters, 1029 (1976).
• 18. Huheey J.E., J. Phys. Chem., 69, 3284 (1965); 70, 2086 (1966).
• 19. Ehrenson S., Brownlee R.T.C. and Taft R.W., Prog Phys. Org. Chem., 10,1 (1973).
• 20. Krygowski T.M., J. Chem. Res.(S), 238 (1984).
• 21. Desiraju G.R. and Steiner T., The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press: Oxford, 1999.
• 22. Jeffrey G.H., An Introduction to Hydrogen Bonding, Oxford University Press: Oxford, 1997.
• 23. Jeffrey G.H. and Saenger W., Hydrogen Bonding in Biological Structures, Springer: Berlin, 1991.
• 24. Sobczyk L., Engelhardt H. and Bunzl K, In: The Hydrogen Bond, Schuster P., Zundel G. and Sandorfy C., Eds.; North-Holland Publ. Comp., 1976, p. 937.
• 25. For the recent review see: Steiner T., Angew. Chem. Int. Ed., 41, 48 (2002).
• 26. Jaskólski M., Polish J. Chem., 58, 9555 (1984).
• 27. Gilli G., Bellucci F. and Bertolesi V., J. Am. Chem. Soc., 111, 1023, (1989).
• 28. Dziembowska T., Polish J. Chem., 72, 193 (1998).
• 29. Grabowski S.J., J. Phys. Org. Chem., 16, 797 (2003).
• 30. Grabowski S.J., J. Phys. Org. Chem., 17, 18 (2004).
• 31. Woźniak K., Krygowski T.M., Kariuki B. and Jones W., J. Mol. Struct., 248, 331 (1991).
• 32. Kortum G., Vogel W. and Andrussow A., Dissociation Constants of Organic Acids in Aqueous Solution, Butterworths: London, 1961.
• 33. The Cambridge Structure Database, the 5.24 version, November 2002, updated July 2003.
• 34. Bondi A., J. Phys. Chem., 68,441 (1964).
• 35. Kenneth R.A., J. Phys. Chem. ^4, 106, 11963 (2002).
• 36. Tehan B.G., Lloyd E.J., Wong M.G., Pitt W.R., Montana J.G., Manallack D.T. and Gancia E., Quant. Struct.-Act. Relat., 21, 457 (2002).
• 37. Iczkowski R.P. and Margrave J.L., J. Am. Chem. Soc., 83, 3547 (1961).
• 38. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery Jr. J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S. and Pople J.A., Gaussian, Inc., Pittsburgh PA 1998.
• 39. Domenicano A., Murray-Rust P. and Vaciago A., Acta. Cryst., 39B, 457 (1983).
• 40. Gas phase electron diffraction, Vilkov L.V., Mastryukova V.S. and Sadova N.I., Determination of the geometrical structure of free molecules, Mir Publisher: Moscow, 1982.
• 41. Allen F.H., Kennard O., Watson D.G., Brammer L., Orpen A.G. and Taylor R., In: International Tables for Crystallography, Vol. C Mathematical, Physical and Chemical Tables, Wilson, A.J.C., Ed., Kluwer Academic Publishers: Dordrecht, Boston, London, 1995, pp. 685-706.